The Torah says quite clearly that: “You shall sit in Succot for 7 days”. This means that one should consider the Succah to be his home and should treat it as such. Thus eating, drinking and sleeping should be in the Succah.
It is very interesting how the various halachic authorities deal with certain issues that crop up with sleeping. One is permitted to eat a snack outside of the succah but is one allowed to take a small nap outside too? The definitive opinion of the Shulchan Aruch is quite clearly that one may not take even a small nap outside. The reason offered by a number of commentators is that sometimes even a little sleep suffices and is considered to be significant.
However, the Pri Megadin stipulates that a nap that lasts less than the time it would take to walk 100 amot (around 50m) is permitted.
It is clear that upon eating a meal in a Succah that one is required to bless “leshev be Succah”. What about sleeping? It seems apparent from various sources that if one intends to enter into a Succah to eat and sleep, then one should make the Bracha on the eating. However, if one enters the Succah in order to sleep alone he should make the blessing prior to doing so.
SLEEPING TODAY IN THE SUCCAH
The Rama points out that many people today do not sleep in a Succah. He cites others who suggest the reason is because of the cold which would make the experience rather unpleasant. He however suggests a different rational to justify the custom; since the Mitzva requires one to live in the Succah like he does in his house, and one’s wife is not obligated to sleep in the Succah, the male is automatically exempt. He does stress however that those who are stringent in the performance of Mitzvot do still today sleep in the Succah.
Ultimately the ruling falls into the hands of the individual and is dependant on his situation. A competent halachic authority should always be consulted.